Sterculic acid

Sterculic acid is a cyclopropene fatty acid. It is found in various plants of the genus Sterculia, including being the main component of Sterculia foetida seed oil.[1]

Sterculic acid
Names
IUPAC name
8-(2-Octyl-1-cyclopropenyl)octanoic acid
Identifiers
3D model (JSmol)
3DMet
1880442
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
C19H34O2
Molar mass 294.479 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Biosynthesis

The biosynthesis of sterculic acid begins with the cyclopropanation of the alkene of phospholipid-bound oleic acid, an 18-carbon cis-monounsaturated fatty acid. This transformation involves two mechanistic steps: electrophilic methylation with S-adenosyl methionine to give a carbocationic reactive intermediate, followed by cyclization via loss of H+ mediated by a cyclopropane-fatty-acyl-phospholipid synthase enzyme. The product, dihydrosterculic acid, is converted to sterculic acid by dehydrogenation of the cis-disubstituted cyclopropane to cyclopropene.[2] An additional step of α oxidation removes one carbon from the carboxy chain to form the 17-carbon-chain structure of malvalic acid.

gollark: I've decided to just update caddy and see if that helps, since I am a bit overdue for switching to v2.
gollark: I have some applications sending data over websocket to the browser - mostly JSON. They work in Chrome and Firefox on Android, but not on Firefox on my Linux systems - it just says "failed to establish connection". Specifically, they work if I run them directly on my local machine but not behind my server's reverse proxy.
gollark: Anyone know a good place to ask about this?
gollark: Also, the webserver doesn't seem to show any accesses happening either.
gollark: I still can't figure out why websockets on my site are behaving weirdly with Firefox and it's very annoying. I may still be using them wrong, but wireshark and mitmproxy don't show *any* request happening when Firefox connects, but do show the other requests for content and stuff.

References

  1. Nunn, J. R. (1952). "The structure of sterculic acid". J. Chem. Soc.: 313–318. doi:10.1039/JR9520000313.
  2. Dewick, Paul (2009). Medicinal Natural products. pp. 46–55. ISBN 9780470741689.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.